Manganese-Catalyzed C(sp²)–H Addition to Polar Unsaturated Bonds

Abstract

Transition-metal-catalyzed nucleophilic C–H addition of hydrocarbons to polar unsaturated bonds could intrinsically avoid prefunctionalization of substrates and formation of waste byproducts, thus featuring high step- and atom-economy. As the third most abundant transition metal, manganese-catalyzed C–H addition to polar unsaturated bonds remains challenging, partially due to the difficulty in building a closed catalytic cycle of manganese. In the past few years, we have developed manganese catalysis to enable the sp²-hydrid C–H addition to polar unsaturated bonds (e.g., imines, aldehydes, nitriles), which will be discussed in this personal account.

1 Introduction

2 Mn-Catalyzed N-Directed C(sp²)–H Addition to Polar Unsaturated Bonds

3 Mn-Catalyzed O-Directed C(sp²)–H Addition to Polar Unsaturated Bonds

4 Conclusion

Key words

manganese - catalysis - C–H activation - polar unsaturated bonds - organic synthesis

Publikationsverlauf

Eingereicht: 23. Februar 2021

Angenommen nach Revision: 27. März 2021

Accepted Manuscript online:
27. März 2021

Artikel online veröffentlicht:
28. April 2021

• References

• 1 Zhang X.-S, Chen K, Shi Z.-J. Chem. Sci. 2014; 5: 2146
• 2 Yang L, Huang H. Chem. Rev. 2015; 115: 3468
• 3 Hummel JR, Boerth JA, Ellman JA. Chem. Rev. 2017; 117: 9163
• 4 Gandeepan P, Muller T, Zell D, Cera G, Warratz S, Ackermann L. Chem. Rev. 2019; 119: 2192
• 5 Wang C. Synlett 2013; 24: 1606
• 6 Liu W, Groves JT. Acc. Chem. Res. 2015; 48: 1727
• 7 Liu W, Ackermann L. ACS Catal. 2016; 6: 3743
• 8 Valyaev DA, Lavigne G, Lugan N. Coord. Chem. Rev. 2016; 308: 191
• 9 Carney JR, Dillon BR, Thomas SP. Eur. J. Org. Chem. 2016; 3912
• 10 Hu Y, Zhou B, Wang C. Acc. Chem. Res. 2018; 51: 816
• 11 Wang Z, Chen L, Mao G, Wang C. Chin. Chem. Lett. 2020; 31: 1890
• 12 Bruce MI, Iqbal MZ, Stone FG. A. J. Chem. Soc. A 1970; 3204
• 13 Zhou B, Chen H, Wang C. J. Am. Chem. Soc. 2013; 135: 1264
• 14 He R, Huang ZT, Zheng QY, Wang C. Angew. Chem. Int. Ed. 2014; 53: 4950
• 15 Zhou B, Ma P, Chen H, Wang C. Chem. Commun. 2014; 50: 14558
• 16 Yang X, Jin X, Wang C. Adv. Synth. Catal. 2016; 358: 2436
• 17 Hu Y, Wang C. Sci. China Chem. 2016; 59: 1301
• 18 Hu Y, Zhou B, Chen H, Wang C. Angew. Chem. Int. Ed. 2018; 57: 12071
• 19 Ali S, Huo J, Wang C. Org. Lett. 2019; 21: 6961
• 20 Hu Y, Wang C. ChemCatChem 2019; 11: 1167
• 21 Jia T, Wang C. ChemCatChem 2019; 11: 5292
• 22 Wang Z, Wang C. Green Synth. Catal. 2021; 2: 66
• 23 Kuninobu Y, Nishina Y, Takeuchi T, Takai K. Angew. Chem. Int. Ed. 2007; 46: 6518
• 24 Zhou B, Hu Y, Wang C. Angew. Chem. Int. Ed. 2015; 54: 13659
• 25 Liu W, Bang J, Zhang Y, Ackermann L. Angew. Chem. Int. Ed. 2015; 54: 14137
• 26 Liang YF, Massignan L, Liu W, Ackermann L. Chem. Eur. J. 2016; 22: 14856
• 27 Liang Y.-F, Massignan L, Ackermann L. ChemCatChem 2018; 10: 2768
• 28 Liu W, Richter SC, Mei R, Feldt M, Ackermann L. Chem. Eur. J. 2016; 22: 17958
• 29 Yu X, Tang J, Jin X, Yamamoto Y, Bao M. Asian J. Org. Chem. 2018; 7: 550
• 30 Wang C, Maity B, Cavallo L, Rueping M. Org. Lett. 2018; 20: 3105
• 31 Kong X, Lin L, Xu B. Adv. Synth. Catal. 2018; 360: 2801
• 32 Kong X, Xu B. Asian J. Org. Chem. 2019; 8: 1862
• 33 Zhou X, Li Z, Zhang Z, Lu P, Wang Y. Org. Lett. 2018; 20: 1426
• 34 Xu Z, Wang Y, Zheng Y, Huang Z, Ackermann L, Ruan Z. Org. Chem. Front. 2020; 7: 3709
• 35 Zheng Q.-Z, Jiao N. Tetrahedron Lett. 2014; 55: 1121
• 36 Huang Z, Lim HN, Mo F, Young MC, Dong G. Chem. Soc. Rev. 2015; 44: 7764
• 37 Sueki S, Wang Z, Kuninobu Y. Org. Lett. 2016; 18: 304
• 38 McKinney RJ, Firestein G, Kaesz HD. Inorg. Chem. 1975; 14: 2057
• 39 Zhou B, Hu Y, Liu T, Wang C. Nat. Commun. 2017; 8: 1169
• 40 Kong X, Xu B. Org. Lett. 2018; 20: 4495
• 41 Liu T, Hu Y, Yang Y, Wang C. CCS Chem. 2020; 2: 749